There’s nothing like a good villain—and I don’t mean a virtuous one. The best villains are often the most unvirtuous, and they delight in being so. They revel in their devilishness, and thoroughly enjoy the path to their goal—whatever it might be. The most fascinating villains can make us laugh, and cringe, and maybe twinge with pity for just a moment. Therein lies the difference between a compelling villain and a real yawner: depth.

We’ve all rolled our eyes at two-dimensional villains, dead-set on world domination. They are driven by little more than the desire to achieve their ultimate goal; these monochromatic villains have no humor, no humanity, no other interests, and usually no motivation or plan beyond “I must rule the world” or whatever his or her obsession is. (“I hate Romeo Montague,” “I must destroy Middle Earth,” “I must kill Peter Pan,” etc.)

Watching scores of single-minded villains launch uninteresting and ultimately-thwarted takeover plans has gotten a little boring. This is perhaps why the anti-hero is such a fulfilling literary character, why anarchic villains like the Joker are so fun to watch, and villains with humanity are so intriguing. One of literature’s most delightfully devilish villains was penned by none other than Shakespeare himself.

Skeptics might think Richard III is just a boring history play, and they’d be half right. It is a history, and the characters featured actually existed. But it is far from boring. When the titular character and protagonist is actually, unabashedly, the villain, you know you’re in for a fun ride. The play begins with Richard slinking onto the stage and delivering his monologue, opening with a delicious pun: “Now is the winter of our discontent made glorious summer by this Son of York.”

From his soliloquy, the audience learns that a long war has just ended, and peace has brought celebrating, cavorting and merriment. But Richard, bemoaning his deformity (conventional reading suggests he’s a hunchback), he despises the time of peace. He is “not shaped for sportive tricks”, and resolves to his make own merriment.

And therefore, since I cannot prove a lover,
To entertain these fair well-spoken days,
I am determined to prove a villain
And hate the idle pleasures of these days.

He’s not mincing words, and moments later confides to the audience that he means to sow discord among his brothers, one of whom is currently king. He weaves his web artfully, winning over the characters with his charm and charisma, and turning to gloat to the audience. This duplicitousness, but more than that the sheer glee with which he plies his two-faced trade, is what makes him so compelling as a villain.

No scene showcases this quite so well as Act I, scene 2. Richard comes upon the widowed Lady Anne, grieving over as her dead father-in-law. This father-in-law—and her husband—were both struck down by Richard on the battlefield. Naturally, Anne despises Richard with a white-hot hatred, and in perhaps one of the greatest conversational sparring matches in all of literature, Anne hurls insult after insult at him. She calls him “foul devil,” “defused infection of a man,” and after spitting on him, exclaims “Would it were mortal poison, for thy sake! . . . Never hung poison on a fouler toad. Out of my sight! Thou dost infect my eyes.”

Meanwhile Richard is trying to woo her! Insisting that it was her beauty that provoked him to murder, that he was moved to kill her husband to free her for a better husband: himself. He expertly parries her verbal blows, and is so convincing, so charming, that by the time Anne leaves the stage, she has agreed to see him again. Without missing a beat, Richard turns to his favored confidante, the audience.

Was ever woman in this humour woo’d?
Was ever woman in this humour won?
I’ll have her; but I will not keep her long.
What! I, that kill’d her husband and his father,
To take her in her heart’s extremest hate,
With curses in her mouth, tears in her eyes,
The bleeding witness of her hatred by;
Having God, her conscience, and these bars
against me,
And I nothing to back my suit at all,
But the plain devil and dissembling looks,
And yet to win her, all the world to nothing!
Ha!

As the play progresses, Richard stirs up conflict and conspiracies on all sides, masterfully puppeteering the members of the court and managing to take the throne. In one poignant scene amongst his counsel, Richard begs God’s pardon on those who wronged his poor brother Clarence. (For those keeping score at home, Clarence was imprisoned in the Tower of London on a false charge laid by Richard, and was murdered in the Tower by a pair of hitmen sent by, you guessed it, Richard.) A member of the court says of Richard’s plea for God’s mercy, “A virtuous and a Christian-like conclusion, To pray for them that have done scathe to us.”

In true two-faced fashion, Richard answers piously “So do I ever”—then aside, to the audience—“being well-advised. For had I cursed now, I had cursed myself.”

When he stands alone on stage at the close of this scene, he recounts all the ways he’s schemed. He boasts of his duplicitousness, and makes this perfectly devilish assessment of himself:

But then I sigh; and, with a piece of scripture,
Tell them that God bids us do good for evil:
And thus I clothe my naked villany
With old odd ends stolen out of holy writ;
And seem a saint, when most I play the devil.

Richard makes good on his promise in the opening scene to prove himself a villain. He orchestrates the deaths of at least 12 others, including his two young nephews, his new wife the Lady Anne, and his loyal (albeit evil) right-hand man. Although he seems to be single-mindedly driven to one goal (attain the crown and keep it), his love for his own villainy sets him apart as one of the greats. He is a villain you love to hate: unscrupulous, manipulative, merciless, and above all remorseless, save for one striking moment.

On the eve of the climactic Battle of Bosworth, he wakes from dreams haunted by those he’s slain. He is shaken, and for the first time, sees himself for what he is.

The lights burn blue. It is now dead midnight.
Cold fearful drops stand on my trembling flesh.
What do I fear? myself? there’s none else by:
Richard loves Richard; that is, I am I.
Is there a murderer here? No. Yes, I am:
Then fly. What, from myself? Great reason why:
Lest I revenge. What, myself upon myself?
Alack. I love myself. Wherefore? for any good
That I myself have done unto myself?
O, no! alas, I rather hate myself
For hateful deeds committed by myself!
I am a villain . . .

Instead of rejoicing that he has achieved his goal and become a villain, he is crestfallen. This moment, when the veil slips and he must face the monster he’s become, is ultimately what makes Richard of Gloucester such a perfect villain. His devolution is complete, his deception shattered, and he realizes that the longest con was on himself.

It’s no wonder then, that his famous final words reveal a frantic, desperate man with nothing to lose:

A horse! a horse! my kingdom for a horse!

Delight in the devilish machinations of a villain with Shakespeare’s Richard III, and enjoy his entire collection of plays and sonnets with The Complete Works of William Shakespeare. Get instant access to his entire body of work, made fully searchable with Noet. Get The Complete Works of William Shakespeare today!

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